アンチマイシンA
WordNet
- the 1st letter of the Roman alphabet (同)a
- the blood group whose red cells carry the A antigen (同)type_A, group A
- a crystalline antibiotic active against various fungi
PrepTutorEJDIC
- answer / ampere
- arsenicの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/17 23:25:00」(JST)
[Wiki en表示]
Antimycin A
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Names |
IUPAC name
(2{R},3{S},6{S},7{R},8{R})-3-[(3-formamido-
2-hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-
1,5-dioxonan-7-yl 3-methylbutanoate
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Identifiers |
CAS Registry Number
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642-15-9 N |
ChEBI |
CHEBI:22584 Y |
ChEMBL |
ChEMBL211501 Y |
ChemSpider |
14246 Y |
InChI
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InChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1 Y
Key: UIFFUZWRFRDZJC-SBOOETFBSA-N Y
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InChI=1/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1
Key: UIFFUZWRFRDZJC-SBOOETFBBB
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Jmol-3D images |
Image |
MeSH |
Antimycin+A |
PubChem |
14957 |
SMILES
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O=CNc1cccc(c1O)C(=O)N[C@@H]2C(=O)O[C@H]([C@H](OC(=O)CC(C)C)[C@H](C(=O)O[C@@H]2C)CCCCCC)C
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Properties |
Chemical formula
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C28H40N2O9 |
Molar mass |
548.63 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is: Y/N?) |
Infobox references |
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Antimycins are a group of secondary metabolites produced by Streptomyces bacteria.[1]
Use
It is the active ingredient in Fintrol, a chemical piscicide (fish poison) used in fisheries management and in the catfish industry.[2]
Mechanism of action
Antimycin A binds to the Qi site of cytochrome c reductase, thereby inhibiting the oxidation of ubiquinol in the electron transport chain of oxidative phosphorylation. The inhibition of this reaction disrupts the formation of the proton gradient across the inner membrane. The production of ATP is subsequently inhibited, as protons are unable to flow through the ATP synthase complex in the absence of a proton gradient. This inhibition also results in the formation of quantities of the toxic free radical superoxide.[3]
It has also been found to inhibit the cyclic electron flow within photosynthetic systems along the proposed ferredoxin quinone reductase pathway.[citation needed]
Fungus-growing attine ants have been shown to use antimycins - produced by symbiotic Streptomyces bacteria - in their fungiculture, to inhibit non-cultivar (i.e. pathogenic) fungi.[4] One research group studying these symbiotic Streptomyces bacteria recently identified the biosynthetic gene cluster for antimycins, which was unknown despite the compounds themselves being identified 60 years ago. Antimycins are synthesised by a hybrid polyketide synthase (PKS)/non-ribosomal peptide synthase (NRPS).[5]
References
- ^ Neft N, Farley TM (March 1972). "Conditions influencing antimycin production by a Streptomyces species grown in chemically defined medium". Antimicrob. Agents Chemother. 1 (3): 274–6. doi:10.1128/aac.1.3.274. PMC 444205. PMID 4558141.
- ^ "Fintrol concentrate". PAN Pesticides Database - Pesticide Products. Retrieved 9 February 2010.
- ^ Dairaku N, Kato K, Honda K et al. (March 2004). "Oligomycin and antimycin A prevent nitric oxide–induced apoptosis by blocking cytochrome C leakage". J. Lab. Clin. Med. 143 (3): 143–51. doi:10.1016/j.lab.2003.11.003. PMID 15007303.
- ^ Schoenian, I. et al. (2011). "Chemical basis of the synergism and antagonism in microbial communities in the nests of leaf-cutting ants". Proc Natl Acad Sci USA 108 (5): 1955–1960. doi:10.1073/pnas.1008441108. PMC 3033269. PMID 21245311.
- ^ Seipke, R.F., Barke, J., Brearley, C., Hill, L., Yu, D.W., Goss, R.G. and Hutchings, M.I. (2011). A single Streptomyces mutualist makes multiple antifungals to support the fungus farming ant Acromyrmex octospinosus. PLoS ONE. In Press
English Journal
- Reduction of molybdate to molybdenum blue by Klebsiella sp. strain hkeem.
- Lim HK, Syed MA, Shukor MY.SourceDepartment of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, University Putra Malaysia, UPM Serdang, Selangor, Malaysia.
- Journal of basic microbiology.J Basic Microbiol.2011 Nov 3. doi: 10.1002/jobm.201100121. [Epub ahead of print]
- A novel molybdate-reducing bacterium, tentatively identified as Klebsiella sp. strain hkeem and based on partial 16s rDNA gene sequencing and phylogenetic analysis, has been isolated. Strain hkeem produced 3 times more molybdenum blue than Serratia sp. strain Dr.Y8; the most potent Mo-reducing bacte
- PMID 22052341
- Honokiol protects osteoblastic MC3T3-E1 cells against antimycin A-induced cytotoxicity.
- Choi EM.SourceDepartment of Food and Nutrition, Education Graduate School, Kyung Hee University, 1, Hoegi-dong, Dongdaemun-gu, Seoul, 130-701, Korea, cheunmi@hanmail.net.
- Inflammation research : official journal of the European Histamine Research Society ... [et al.].Inflamm Res.2011 Nov;60(11):1005-12. Epub 2011 Jul 29.
- OBJECTIVE: Honokiol is a phenolic compound isolated from the bark of Magnolia officinalis, a plant widely used in traditional medicine. Antimycin A, which inhibits complex III of the electron transport system, has been used as a reactive oxygen species generator in biological systems. In the present
- PMID 21800176
Japanese Journal
- Neuroprotective effects of VCP modulators in mouse models of glaucoma
- 肝微小循環の酸素勾配を模倣する培養マイクロデバイスの開発と代謝酵素の発現解析
- First Total Synthesis of Neoantimycin
Related Links
- Buy Antimycin A (CAS 1397-94-0), an antibiotic that induces apoptosis, from Santa Cruz Biotechnology. Purity: ≥95% ... Antimycin A is an antibiotic that induces apoptosis and inhibits the mitochondrial electron transport chain from ...
- Sigma-Aldrich offers Sigma-A8674, Antimycin A from Streptomyces sp. for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Frequently Asked Questions Live Chat and Frequently Asked Questions ...
★リンクテーブル★
[★]
- 英
- electron transport chain, electron transport system, electron-transport system, electron-transfer system
- 関
- 電子
電子伝達系
分子
還元力のキャリアー
酵素複合体
- CoQによるNADHの酸化を触媒
- シトクロムcによるCoQの酸化を触媒
- 電子受容体O2による還元型シトクロムcの酸化を触媒
- CoQによるFADH2の酸化を触媒
反応
- NAD+ + 2H+ + 2e- ⇔ NADH ΔE = -0.315V
- 反応は左に進む
- 1/2O2 + 2H+ + 2e- ⇔ H2O ΔE = 0.815V
- 反応は右に進む
- NADH + 1/2O2 + H+ ⇔ H2O + H2O ΔE = 1.130V
- ΔG゚'=-nFΔE゚' ゆえに ΔG゚' = -218kJ/mol。ATP合成には30.5kJ/mol必要
- 1モルのNADHの酸化により約3ATPを合成できる
阻害薬 (FB.337)
[★]
- 英
- antimycin A
- 関
- 電子伝達系
- 同
- antimycin A
[★]
[★]
- 関
- adenoviral、adenovirus